Methanol → HCID 69515448, compound

HRID 1767451Notes

Reaction equation

HRID 1767451 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH:21]([CH2:26]Br)[C:22]([O:24][CH3:25])=[O:23].C(=O)([O-])[O-].[K+].[K+].CO>CN(C)C=O.C(OCC)(=O)C.O>[CH3:25][O:24][C:22]([CH:21]1[CH2:26][N:12]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:11][CH2:10][CH2:9][N:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:23]

Participants

8

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 95428Methyl 2,3-dibromopropionateHCID 151498N,N'-Bis(benzyl)-1,3-diaminopropane

Product 1

HCID 69515448HCID 69515448, compoundYield 7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,N′-Dibenzylpropane-1,3-diamine (Sandstroem, J. et al, Tetrahedron; EN; 34; 1978; 371-378) (2.0 g, 7.86 mmol), methyl 2,3-dibromopropionate (1.28 ml, 7.86 mmol), and potassium carbonate (2.17 g, 15.72 mmol) were dissolved in dry dimethylformamide (125 ml) and methanol (20 ml) and the mixture was heated to reflux for 6 days. The reaction mixture was allowed to cool to room temperature and water (200 ml) and ethyl acetate (200 ml) were added. The aqueous layer was extracted with 2×200 ml of ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered and the solvent was evaporated. The crude product was purified by chromatography on silica, using a mixture of ethyl acetate and heptane 1:6 as the eluent. Fractions containing the product were evaporated, to afford 180 mg of 3A as an clear oil in 7% yield.

Workup

  1. temperatureto reflux for 6 days
  2. extractionThe aqueous layer was extracted with 2×200 ml of ethyl acetate
  3. dry with materialthe combined organic layers were dried with sodium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe crude product was purified by chromatography on silica
  7. additiona mixture of ethyl acetate and heptane 1:6 as the eluent
  8. additionFractions containing the product
  9. customwere evaporated

Sources & evidence

ORD record
ord-82e1499e677245e5ae11e373ce3b097d
Source dataset
uspto-grants-2007_06
Patent number
US07235538B2

Reaction notes

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